Efficient routes towards a series of 5,5'-bithiazolidinylidenes as π-electron acceptors.

نویسندگان

  • Y Le Gal
  • D Ameline
  • N Bellec
  • A Vacher
  • T Roisnel
  • V Dorcet
  • O Jeannin
  • D Lorcy
چکیده

Different approaches have been studied in order to prepare efficiently the sulfur rich electron acceptor, DEBTTT. Among the various routes used, the one going through the synthesis of a bicyclic derivative, where the thiazole-2-chalcogenone is fused with a 1,3-dithiole-2-one, leads to the target molecule under milder conditions and better yield. Thus, this approach has been explored for the synthesis of a series of acceptors either by modifying the substituent on the thiazole core or by changing the exocyclic chalcogen atoms. All these sulfur rich electron acceptors exhibit short intra- and intermolecular SS contacts in the solid state. Electrochemical investigations show that the nature of the exocyclic chalcogen atom of the thiazole ring has a significant influence on the accepting ability as a cathodic shift of about 220 mV is observed just by changing sulfur for oxygen. This structural modification enables the tuning of the redox properties.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 13 31  شماره 

صفحات  -

تاریخ انتشار 2015